US4140707A - Malonato platinum anti-tumor compounds - Google Patents

Malonato platinum anti-tumor compounds Download PDF

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Publication number
US4140707A
US4140707A US05/778,955 US77895577A US4140707A US 4140707 A US4140707 A US 4140707A US 77895577 A US77895577 A US 77895577A US 4140707 A US4140707 A US 4140707A
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sub
platinum
compounds
tumor
malonato
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Michael J. Cleare
James D. Hoeschele
Barnett Rosenberg
Loretta L. Van Camp
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RESEARCH Corp TECHNOLOGIES Inc 6840 EAST BROADWAY BLVD TUCSON AZ 85710 A NOT-FOR-PROFIT NON-STOCK CORP OF
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0086—Platinum compounds
    • C07F15/0093—Platinum compounds without a metal-carbon linkage
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention relates to novel malonato platinum coordination compounds and to their use in cancer chemotherapy.
  • the invention provides platinum coordination compounds having the formula:
  • R and R 1 are selected from the group consisting of H, lower alkyl, aryl, aralkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxy, OH, or are combined with the carbon atom to form a cycloalkyl or cycloalkenyl group, and substituted derivatives thereof;
  • L is a bidentate anionic ligand
  • L is a monodentate anionic ligand.
  • the invention also relates to a composition and method for treating malignant tumors in animals comprising parenterally administering to an animal affected with a malignant tumor a solution containing a platinum coordination compound as defined hereinabove in an amount sufficient to cause regression of the tumor.
  • Platinum (II) forms dsp 2 coordination compounds which have a square planar arrangement in space.
  • Platinum (IV) forms d 2 sp 3 coordination compounds which have an octahedral arrangement in space.
  • the coordination compounds of the invention include the cis and trans isomers of platinum (II) and platinum (IV) which contain the bidentate malonato ligand which may be substituted or unsubstituted.
  • the malonato ligand may contain substituents selected from the group consisting of lower alkyl, (e.g., methyl, ethyl, n-propyl, isopropyl, n-butyl, etc.); aryl, (e.g., phenyl; lower alkyl-, lower alkenyl-, halo-, nitro-, lower alkoxy-substituted phenyl and naphthyl); aralkyl, (e.g., phenylmethyl (benzyl), 2-(1-naphthyl)methyl); alkenyl, (e.g., 4-amino-1-butene, allyl); cycloalkyl, (e.g., cycloprop
  • 1,1-cycloalkylenedicarboxylic acids e.g., 1,1-cyclopropanedicarobxylic acid, 1,1-cyclobutanedicarboxylic acid, etc.
  • 1,1-cycloalkenyldicarboxylic acids e.g., 1,1-cyclopropenedicarboxylic acid, 1,1-cyclobutenedicarboxylic acid, etc.
  • the coordination compounds of the invention also contain two monodentate ammonia or primary or heterocyclic amine ligands, i.e., when x in the above formula is 2 or one bidentate amine ligand, i.e., when x is 1.
  • Suitable monodentate amine ligands include lower alkyl amines, (e.g., methyl-, ethyl-, n-propyl-, isopropyl-, n-butyl- amines, etc.), aryl amines, (e.g., aniline), aralkyl amines, (e.g., benzylamine), hydroxy lower alkyl amines, (e.g., ethanolamine, propanolamine, etc), hydroxylamine, lower alkoxy amines (e.g., methoxylamine, etc.), alkoxyalkylamines (e.g., methoxymethylamine, etc.), and heterocyclic amines (e.g., pyridine and aziridine).
  • lower alkyl amines e.g., methyl-, ethyl-, n-propyl-, isopropyl-, n-butyl- amines,
  • R 7 --CHNH 2 --COOH wherein R 7 is H, lower alkyl (e.g., methyl, isopropyl, etc.), hydroxy lower alkyl (e.g., hydroxymethyl, hydroxyethyl, etc.), aralkyl (e.g., benzyl, etc).
  • coordination compounds of the invention may include two identical or different monodentate ligands.
  • Suitable bidentate amine ligands include the substituted and unsubstituted primary and secondary ethylenediamines.
  • One or both of the carbon atoms of the ethylenediamine may contain substituents such as lower alkyl (e.g., methyl, ethyl), hydroxyl, alkoxy (e.g., methoxy, ethoxy, etc).
  • Secondary ethylenediamines wherein one or more of the amine groups contains substituents such as listed above for the carbon atoms of the primary amine and aryl (e.g., phenyl) and aralkyl (, e.g. benzyl) may also be utilized.
  • Pt (II) coordination compounds specified herein do not exist as geometrical isomers; however, the Pt (IV) compounds exist as cis and trans isomers. It is to be further understood that the invention is inclusive of the cis and trans isomers.
  • Suitable monodentate anionic ligands include chloride, bromide, iodide, nitrite, hydroxide, nitrate, sulfamate, etc.
  • bidentate anionic ligands which may be present are oxalate, pyrophosphate, dithioxalate.
  • the invention includes those coordination compounds containing mixed monodentate anionic ligands.
  • the preferred compounds are those wherein R and R 1 in the above formula are H, methyl or ethyl, i.e., malonatoplatinum, methylmalonatoplatinum and ethylmalonatoplatinum coordination compounds.
  • the coordination compounds of the invention may be prepared by one of a variety of well-known methods.
  • a general method of preparation of the Pt (II) coordination compounds is as follows: Starting compounds having the formula cis-[Pt A(Hal) 2 ] wherein Hal is I, Cl or Br and A is one bidentate or two monodentate amine ligands (prepared by the method of S. C. Dhara, Indian J. Chem., Vol 8, p. 193 (1970)) are reacted with silver nitrate to form the diaquo complex. The latter is then reacted with the malonate ion to form the coordination compounds of the invention.
  • This method is represented by the following reaction scheme:
  • A is one bidentate amine ligand or two monodentate amine ligands.
  • silver nitrate 22.55g -- slightly less than the stoichiometric amount in order to avoid silver contamination
  • water 50 ml.
  • [Pt(NH 3 ) 2 Cl 2 ] 20g
  • the contents were warmed (60° C.) on a hot plate with rapid stirring until the silver chloride precipitation was complete and the mother liquor was almost colorless.
  • the silver chloride was filtered off using a fine pore sintered glass filter and the precipitate was washed several times with hot water to give a total filtrate volume of 100-200 ml.
  • the product was recrystallized by dissolving in boiling or near boiling water.
  • the above yield (20.5g) required about 3 liters of boiling water for complete dissolution.
  • Malonic acid 1g/L was dissolved in the water to suppress any hydrolysis.*
  • the filtered solution was cooled to 0° C. to give white fluffy needles (18.25g-83%).
  • the crystals decompose between 185°-190° C.
  • the structure of the product was verified cia an i.r. spectrum. Solubility of the product is low in cold water, i.e., 20 mg/100 mls at 20° C. and 43 mg/100 mls at 37° C., but higher in near boiling water (90°-100° C.) ⁇ 65g/100 ml.
  • Silver nitrate (3.64g) was dissolved in 20 ml of water and added to [Pt(NH 2 ) 2 (CH 2 ) 2 CL 2 ] (3.5g) suspended in water (30 ml.) in a conical flask. The mixture was stirred on a warm hot plate for 5-10 minutes until all the yellow platinum complex had dissolved to give a yellow liquor plus a copious white silver chloride precipitate. The mixture was filtered through a fine pore filter and the precipitate washed twice with small volumes of hot water. The clear filtrate plus washings was added to an aqueous solution of methylmalonic acid (2g in 20mls) which had been adjusted to pH 5-6. The mixture was heated to about 80° C.
  • a second crop (0.33g-8%) was obtained by reducing the bulk of the mother liquor.
  • Silver nitrate (5.45g) was dissolved in water (30 ml) and added to trans [Pt(NH 3 ) 2 Cl 4 ] (3g) suspended in water (30 mls) containing concentrated nitric acid (3 ml). The contents were warmed on a hot plate (70°-80° C.) and stirred for at least one hour. The mixture was filtered through a fine pore sintered glass filter to remove the silver chloride. The precipitate was washed twice with a small volume of hot water. The clear filtrate plus washings was tested with a drop of 1M KCl solutions to determine if excess silver chloride was present.
  • the malonate group is shown to be coordinated to the platinum by the observed change in the electronic spectra on going from the aquo to the malonate species.
  • structures such as [Pt(NH 3 ) 2 (H 2 O) 2 ] 2 (H 2 C 3 O 4 )] are ruled out confirming the analytical data.
  • zero-time conductivity measurements support a neutral compound.
  • the i.r. spectra show the presence of coordinated carboxyl groups (1600-1650 cm -1 and 1400 cm -1 ) with no CO 2 H groups (which would show at 1700-1750 cm).
  • the carboxyl group vibrations are compatible with a chelated structure as compared to oxalate complexes of known structures.
  • the compounds of the invention were tested for anti-tumor activity using our standard screening tumor, solid sarcoma 180 tumer in female Swiss white mice, following standard protocols for this testing as set by the National Cancer Institute. (Cancer Chemotherapy Rep., 25(1962)).
  • mice For these tests an S 180 tumor taken from a sacrificed mouse was disected free of superfluous tissue and cut under sterile conditions into approximately 10 milligram size pieces. These tissue pieces were then implanted by trocar in the left axillary region, subcutaneously, in new mice. The mice were, on the average, approximately four weeks old and weighed 18-20 grams. Taking day 0 as the day of implant, the animals were sacrificed on day 10. The tumors were excised and weighed and the ratio of the weights of the tumors in mice in the treated animals to the control set of animals was obtained. This ratio, multiplied by 100, is given as the T/C ratio in Table I.
  • the coordination compound was freshly dissolved in sterile distilled water and injected intraperitoneally on day 1 into each of the test mice.
  • the volume of the injection was usually 1/2 ml.
  • a fine dispersion was prepared of the dose needed for the test.
  • some of our test results were obtained on animals where a slurry of the compound was injected. These are so noted in Table I below.
  • the malonatoplatinum coordination compounds of the invention are preferably dissolved or suspended in water or other pharmaceutically acceptable carrier liquids.
  • the parenterally administerable composition should preferably contain from about 0.5mg to about 10mg per ml., it being understood that the amount may vary greatly depending upon the particular compound employed and the animal to be treated.
  • the platinum coordination compounds of the invention are preferably administered parenterally to an animal affected with a malignant tumor.
  • the duration of treatment and the dose level will depend in each case upon the size of the host animal, nature and size of the tumor, etc. Generally, however, a dose level of from about 20 to about 200 mg/kg of body weight per day will be sufficient. It is to be understood, however, that the platinum coordination compounds compounded with a suitable pharmaceutical carrier in the same proportions as recited above may also be administered orally at the same dosage levels.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US05/778,955 1972-06-08 1977-03-18 Malonato platinum anti-tumor compounds Expired - Lifetime US4140707A (en)

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JP (1) JPS5629676B2 (el)
CA (1) CA1023759A (el)
CH (2) CH588505A5 (el)
DE (1) DE2329485C3 (el)
FR (1) FR2187345B1 (el)
GB (1) GB1380228A (el)
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SE (2) SE415182B (el)

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FR2187345A1 (el) 1974-01-18
GB1380228A (en) 1975-01-08
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US4140707B1 (el) 1989-12-19
SE7810577L (sv) 1978-10-10
NL930049I1 (nl) 1993-09-01
JPS5629676B2 (el) 1981-07-09
CH605550A5 (el) 1978-09-29
NL183724C (nl) 1989-01-02
FR2187345B1 (el) 1976-12-31
JPS4948621A (el) 1974-05-11
DE2329485B2 (de) 1979-11-22
CA1023759A (en) 1978-01-03
NL930049I2 (nl) 1993-11-16
DE2329485A1 (de) 1973-12-20
NL183724B (nl) 1988-08-01
DE2329485C3 (de) 1980-07-31
SE415182B (sv) 1980-09-15

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